반응 #91020

반응 방정식

tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

tert-Butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

boron trichloride

water

NaHCO3

→

4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid

수율 24.0%

용매

DCM

DCM

반응 조건

후처리

1. 1
   workup.WAITat RT for 2 h
2. 2
   온도The reaction mixture was cooled to 0° C.
3. 3
   여과The resulting white precipitate was collected by filtration
4. 4
   세척washed with water (2 mL)
5. 5
   기타The solid was dried
6. 6
   기타purified by capture and release on SAX
7. 7
   세척eluting with 5% AcOH in THF

실험 절차

A solution of tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate (5) (55 mg, 0.13 mmol) in DCM (5 mL) was cooled to 0° C. and treated dropwise with a solution of 1 M boron trichloride in DCM (349 μL, 349 μmol). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction mixture was cooled to 0° C. and water (0.5 mL) and sat. aq. NaHCO3 (2 mL) were added. The resulting white precipitate was collected by filtration and washed with water (2 mL). The solid was dried, then purified by capture and release on SAX, eluting with 5% AcOH in THF to afford 4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid (AAA-057) (11 mg, 24%) as a white solid: m/z 370 [M+H]+ (ES+), 368 [M−H]− (ES−); 1H-NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, s), 8.06 (2H, s), 7.76 (1H, d), 7.48 (1H, d), 7.28 (1H, dd), 4.14 (2H, q), 1.91 (1H, s), 1.40 (3H, t), 1.35 (1H, s).

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